


Dean and Castiel Do the Best Friend Tag

by Pippiuscattius



Series: SPN Characters Do Various Tags [1]
Category: Supernatural
Genre: Best Friends, Castiel and Dean Winchester Being Idiots, Castiel and Dean Winchester Need to Use Their Words, Castiel and Dean Winchester are Cute, Castiel and Dean Winchester are Dorks, Castiel in the Bunker, Castiel is a Good Friend, Charlie is alive, Charlie ships Destiel, Cutesy, Dean is Bad at Feelings, Fluff, Humor, I am a smol bean who loves fanfiction and Destiel, M/M, Men of Letters Bunker, Mentions of Many Past Episodes, My roommate helped me with these tags so shoutout to her, Pre-Relationship, Video Cameras, best friend tag
Language: English
Status: Completed
Published: 2018-01-25
Updated: 2018-03-03
Packaged: 2019-03-09 05:21:57
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 78
Words: 16,879
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13474539
Author URL: https://archiveofourown.org/users/Pippiuscattius/pseuds/Pippiuscattius
Summary: One video camera. Two oblivious dorks in love. Seventy-seven questions about their totally platonic relationship.Bring it on.





	1. Introduction

**Author's Note:**

> This is probably really silly but haaaaa I don't care I had fun writing it. I'm planning to divide the questions up into chapters. Some will be long, some will be short, just however they gotta be. I'm not sure what you'd call this format; it's basically like a freeform style screenplay. 
> 
> This is set somewhere in season 11 before Casifer happens, or at least that's what I vaguely had in mind when I wrote these.
> 
> Here's a link to the list that I used: https://whyvideoisgreat.com/best-friend-tag-questions-list

[Camera screen comes into focus. Dean and Castiel are seated at a table. Dean is leaning off screen while Castiel stares inquisitively into the camera.]

Dean: [Mumbling, barely audible] Do we really have to…? I don’t get why… [Defeated sigh] Fine.

[Dean slips fully into frame, warily looking into the camera. He eventually waves a single hand but doesn’t regard the camera with any other degree of friendliness.]

Dean: Alright, so...let it be noted that we’re being forced to do this against our will. I’m Dean, this is Cas, and we’re doing the…“best friend tag,” or something like that. Yadda yadda yadda, intro’s done. Let’s get this over with.

[Dean takes a piece of paper with a list of printed questions and holds it out so that he and Castiel can read it. Castiel keeps his stern attention on the paper as he curiously reads over its contents.]

Castiel: I’m not sure I understand the purpose of this exercise.

Dean: You think I do? All I know is, the sooner we get through this list, the sooner we’ll get those vouchers for all-you-can-eat dessert at that buffet. Their pie is like, the best in town.

Castiel: [Nodding, but not really understanding] We are required to answer all of these?

Dean: Suppose so. Let’s get to it; those pies are calling out my name.


	2. Question #1: How and when did you and your best friend meet?

Dean: Easy. You burst into that barn after you “raised me from perdition” or however you said it and showed off your wings.

Castiel: I recall that. You stabbed me in the chest.

Dean: Just goes to show that first impressions aren’t everything, eh?

Castiel: I must correct your answer, though. Our first meeting did not occur in that barn; it occurred in Hell when I rescued your soul.

Dean: …Oh, uh…I don’t remember that.

Castiel: You wouldn’t. Your soul likely blocked out the memory due to the trauma you experienced while still in Hell.

Dean: [Not sure how to feel about something as deep and traumatic as his Hell memories being brought up so soon into innocent conversation] W-well, that doesn’t count, since I don’t remember. Barn it is.

Castiel: You may know our meeting in that barn as our first, but for me it will always be when I discovered your soul in Hell. I’d think that due to our unique circumstances, this question has two answers.

Dean: [Getting antsy] Alright, sure, whatever keeps your wings from gettin’ all ruffled.


	3. Question #2: What was your first impression of them?

Dean: Well, for starters, I thought Cas was a monster.

Castiel: Looking back, I can’t particularly place any blame upon you for making that assumption. My entrance was…a tad over-the-top.

Dean: But outside of that, I gotta say, I didn’t trust him. Hunter’s instinct, you know? Didn’t take long for me to realize he wasn’t so bad though, especially compared to the rest of his wackadoodle family.

Castiel: Speaking from my own experience, my first impression of you, or rather your soul in Hell, was that you were unjustly tortured and in need of saving. Upon closer contact however, I was surprised by how strong and vibrant your soul remained despite the conditions it had been put through. Even if I was a much different angel then than I am now, I found that to be extremely admirable. Rarely is such a thing seen among the tormented souls of Hell.

Dean: [A bit flustered and trying his hardest to hide it] I’ll, uh, take that as a compliment, then.

Castiel: [Proudly] It was intended as such.


	4. Question #3: What’s your favorite memory together?

Dean: [Laughing] Oh yeah, I definitely know the answer to this one. [Smirks at Castiel] Remember Chastity?

Castiel: [Quickly getting nervous] I…do recall my encounter with Chastity, yes.

Dean: I still cannot _believe_ you made her run off. You were alone with her for, what, several seconds? [Starts laughing again as he recalls the scene]

Castiel: [Turning a bit red and looking away] That was not one of my more tactful moments. [Regaining a semblance of confidence] I personally think that it turned out for the best, in any case. I preferred to maintain my own chastity, and you seemed to get much amusement from my blunder.

Dean: [Still laughing] No kidding! I hadn’t laughed that hard in _years_!

Castiel: So you told me at the time. [Quietly pondering something while Dean continues to laugh to himself] Even if it is a prime example of my often-poor social skills, it is one of my fonder memories as well. At no other point had I ever seen you openly express so much joy; with the weight of the end of the world on your shoulders, you allowed such little room for your own enjoyment.

Dean: [Has finally stopped laughing, but still grinning like an idiot] Yeah, well, thanks for that whole thing. I needed a good laugh right about then. Just, uh…don’t go soliciting any more prostitutes with daddy issues for my amusement, alright? It’d get old pretty fast.

Castiel: [A bit perplexed] I…wasn’t planning on it. I doubt it would produce the same results anyways.

Dean: [Abruptly rushing to move on from this topic] Good. What’s next?


	5. Question #4: Describe each other in one word.

Castiel: [Tilting his head as he reads the paper] That is not a question. That is a statement.

Dean: Just roll with it, Cas. [Leans back in his chair as he thinks of an answer] Man, I dunno. I guess “angel?”

Castiel: [Unamused] That is merely my species. If I were to describe you as “human,” would that encompass your entire personality?

Dean: Yeah, okay, I get it… [Snaps his fingers] Oh, no, wait, I’ve totally got it. “Dork.”

Castiel: What exactly does being a “dork” mean? You’ve used that title for me numerous times before, but I have never fully understood its meaning.

Dean: Means you’re…I dunno, dorky!

Castiel: That doesn’t particularly clear up my confusion.

Dean: Dorks are… [Throwing his hands up] I dunno, just, themselves! They have this way about ‘em, like they don’t really care what anyone else thinks, so they act true to who they actually are.

Castiel: [Faintly smiling] That sounds like a nice title, then.

Dean: And they’re also kinda clumsy and weird, don’t really act the way most people would without realizing it, you know?

Castiel: I suppose that would be accurate to my persona… [Grumbling to himself] Although I hardly think I’m “weird.”

Dean: Well, you are. [Realizes that may have sounded harsh] I-I mean, in a good way, though. Bein’ a dork is usually a good thing.

Castiel: I’ll take your word for it. As for a single word to describe you…

Dean: Oh boy. Lemme guess, something super dorky? ‘Cause you’re a dork?

Castiel: [Smiling and losing his concentration at Dean’s continued use of “dork”] I was thinking more along the lines of…hero.

Dean: [Genuinely surprised] Hero…? Seriously?

Castiel: Yes, Dean. That’s truly what you are. [Holds up a hand before Dean can say anything else in response] And before you go on a wholly unnecessary self-loathing tirade, let me assure you that I have seen directly into your soul and I know for an exact fact that “hero” defines you even down to your core.

Dean: [Raring to object, but he finds himself unable to] Well, uh…alright, whatever, next question.

[Castiel smiles in satisfaction]


	6. Question #5: What is your best friend’s dream job?

Dean: [Shrugging] You seem to like bees and flowers a lot. I could really picture you as a gardener, or maybe a beekeeper. Hell, you’d probably be both.

Castiel: [Absently nodding his head] Yes, I would greatly enjoy those professions…

Dean: See, this is why you’re a dork. ‘Cause you love bees and flowers and… [Scrunches up nose] …stuff.

Castiel: I would say that makes me a naturalist more than anything else.

Dean: Yeah, a dorky naturalist.

Castiel: [Ignoring Dean’s continued use of his title] Although I know you find satisfaction in your life as a hunter, I’m fairly certain that you would prefer a more domestic profession. You would make an excellent automobile mechanic with your mechanical talents and affinity for cars.

Dean: Dude, that would be sweet! [Getting ahold of his rush of excitement] But uh, you know, yo ho, yo ho, a hunter’s life for me.

Castiel: I thought that “yo ho” was a phrase used by human pirates?

Dean: Y-yeah, it is but I was just…nevermind, it’s another reference that went over your head.


	7. Question #6: What is something that annoys you about the other person?

Dean: All things considered, you’re pretty easy to work with, actually…but…

Castiel: “But…?”

Dean: _Man_ are you stubborn sometimes. And other times, you can be so overly-idealistic about stuff…it’s a nice thought, but you gotta remember, the hunting life rarely turns out all lollipops and roses.

Castiel: [Solemnly] I have tried to keep that in mind…angels naturally see the world in black-and-white terms, and though we may oversimplify far more complex issues, many of us mean well. I cannot blame you for faulting me, though. I have essentially broken the world through my misguided intentions on more than one occasion…

Dean: [Feeling guilty at having brought this up] But, y-ya know, if you’re gonna have any faults at all, they may as well be from good intentions! You’ve always done what you think is truly right, and even if that doesn’t turn out the way it’s supposed to, that’s friggin’ admirable.

Castiel: [Brightening somewhat at Dean’s words] Thank you, Dean.

Dean: [Squarely facing Castiel] Now c’mon, hit me with your best shot.

Castiel: [Extremely concerned] Why…would you want me to hit you? [Realizing] Is this another product of your rampant self-loathing complex? Because I refuse to play into it.

Dean: No, I meant… [Sighing] Don’t hold back talkin’ about whatever it is about me that annoys you.

Castiel: Oh…I see. [Taking on a business-like stance] Well, your self-loathing complex would be an excellent starting point, seeing as it is unwarranted and brings distress to me and everyone around you. This in turn plays into your self-sacrificial tendencies, which although heroic in nature bring me intense, undue stress. And if you think that _I’m_ stubborn, perhaps you should take the time to look into a mirror on occasion.

Dean: …You done?

Castiel: Yes, I have aired my most outstanding grievances.

Dean: [Clapping his hands together] Alright, let’s get moving right along, then.

Castiel: You do not wish to discuss any of what I have said?

Dean: [Dismissively] No, not really.

Castiel: [Quietly to himself] A prime example of your stubbornness…


	8. Question #7: If you and your best friend could live anywhere in the world together, where would it be and why?

Dean: I’m pretty happy having you here in the bunker, honestly. But if I could pick anywhere _else_ in the world to live…

Castiel: Although it may not be your favorite place per se, heaven would be a lovely place for all of us to stay. You and Sam have your own heaven there, and I would be content to stay there alongside you both.

Dean: [Dismissively waving a hand] Heaven’s technically not part of the world. ‘Sides, that’s for the afterlife. I’m thinkin’ about right here, right now.

Castiel: Well then where on earth would you like to live? I will happily follow you to any end of the planet that you so desire.

Dean: Even if I settle in another “den of iniquity?”

Castiel: …If that is what you wish, then so be it.

Dean: [Chuckling somewhat] Luckily for you, I had something else in mind. Somewhere on the coast might be nice…Louisiana? New Orleans? Now those people know how to party!

Castiel: New Orleans is an interesting choice…there would be no shortage of cases. Ghosts and witches are located throughout the city.

Dean: Right, yeah! And Sammy would love all the nerdy historical stuff there too!

Castiel: So we’re settling on New Orleans?

Dean: For now, yeah. We ought to plan a trip there sometime anyways…like you said, cases abound down there. Remind me to bring it up to Sam next time I see him.

**Notes for the Chapter:**

> I visited New Orleans for the first time recently, and the whole time I was there, I couldn't stop thinking about how much I wanted a Supernatural episode set there. It's like...the perfect setting. That's what inspired this bit.
> 
> Coincidentally, I actually ran into a CW film crew on the street while I was there. They weren't filming SPN, they were filming The Originals, but it still made me stop and think.


	9. Question #8: What is your favorite inside joke that you and your best friend share?

Dean: [Turns to Cas and smirks deviously] Hey, Cas. Your dad’s not around much, is he?

Castiel: [Wondering why the heck this is being brought up] Um…no, he isn’t. God disappeared years ago and no one has seen him since. You know this, Dean.

Dean: Right, right. Say, you know it’s not your fault, right? He just ran off ‘cause he hated his job at the post office.

Castiel: [Finally figures out what Dean’s referencing] You are still referring to my encounter with Chastity, are you not?

Dean: [Breaking out into laughter] I will _always_ refer to your encounter with Chastity!


	10. Question #9: Who takes longer to get ready in the morning?

Castiel: Seeing as I do not have to “get ready” in the morning at all, Dean is the answer by default.

Dean: Hey wait a minute, that’s not fair! When you were human I bet you took forever to get ready! [Vaguely gestures to Castiel’s hair] Had to get your hairdo in order if nothing else.

Castiel: Relatively speaking, I recall being rather quick to prepare in the morning during my time as a human. I had to be quick; I was on the run from other angels.

Dean: [Face falling] Oh…right…would’ve been nice if you could’ve stayed in the bunker during that.

Castiel: Gadreel had good intentions when he forced you to force me to leave. It’s in the past regardless. [Pauses] And between the two of us, you are still the one who takes longer to get ready in the morning.

Dean: _Fine_ , whatever. I take longer to get ready in the morning. But I’m still faster than most humans!


	11. Question #10: What’s your best friend’s favorite season?

Dean: Definitely gotta be Spring. That’s when flowers and bees and nature are all over the place.

Castiel: That would be correct. Spring is easily my favorite of the earthly seasons. It is the high point of the cycle of life and growth, when my father’s creation is at its pinnacle potential and beauty.

Dean: [Coughing into his fist] Alright, flower boy. What about me? Do you remember what my favorite season is? I told you once.

Castiel: [Confidently] I remember. You said that autumn was your favorite season.

Dean: You could just call it fall, ya know. But yeah, that’s right! Because… [Waits for Castiel to finish his sentence]

Castiel: Because…pie.

Dean: Because _pie_! Atta boy! [Claps him on the back]


	12. Question #11: What’s your best friend’s favorite song?

Castiel: Dean enjoys many songs belonging to the classic rock genre. But…I am not sure which one would be his favorite.

Dean: Can’t fault you for that. Hell, I don’t think I can pick just one. It’s gotta be between “Ramble On” and “Travelling Riverside Blues.”

Castiel: We could peruse your library of cassettes in the Impala to decide between them.

Dean: Later. Remember, the sooner we get this done, the sooner we get free pie!

Castiel: Right…the pie. Can you name my favorite song?

Dean: [Troubled] I…don’t think you’ve ever mentioned any of your music tastes.

Castiel: I suppose I never shared it with you, but I find particular enjoyment in what humans call “classical” music.

Dean: [Stares for a few moments] Dude. Really?

Castiel: Yes, Dean. I find the instrumentation of many of the classical artists of earth’s past to be incredibly relaxing and well-crafted. The rhythm synchronizes quite well with my wavelengths in a way that other music rarely does.

Dean: [Unable to hide a grin] And here is yet more irrefutable evidence that you are, in fact, a huge dork. Which song’s your favorite?

Castiel: Although I enjoy many classical orchestrations…Beethoven’s Moonlight Sonata is the one I find myself revisiting the most frequently. It’s in tune with my celestial wavelengths to a near perfect degree.

Dean: The more I think about it, the more perfect that seems for you. I’m not always one for the oldies, least not when they’re _that_ old, but good on you.


	13. Question #12: What is your best friend’s favorite band?

Castiel: I would venture to say that your favorite band is a classic rock band?

Dean: Damn straight! Question is, which one’s my fav…

Castiel: You listen to that one, Ack Slash Dic, a lot.

Dean: [Not understanding Castiel at all] …Ack…Slash… [His eyes widen] Oh! You mean AC/DC! [Laughs for a few moments] Dude, that is…that is priceless, oh god…

Castiel: [A little frustrated by his mistake, but he brushes past it] No matter how it’s pronounced, is it your favorite?

Dean: Could be…but then again, you can’t beat Zeppelin…

Castiel: [Plainly] You can’t decide.

Dean: …Yeah. We’re definitely gonna have to look back through my cassettes to figure that out. What about you, huh? Which old dude in a powdered wig is your favorite musician? Mozart? Beethoven? Chivekovsky?

Castiel: _Tchaikovsky_ , Dean. And although I enjoy all of their work, Beethoven’s is the most in tune with the spheres, so his work is my favorite.

Dean: I…have no idea what that means, but alright, you dork.


	14. Question #13: What is your best friend’s favorite animal?

Dean: Bees. Just…bees.

Castiel: Their social hierarchy and system of living are among one of the most complex in the animal kingdom. I find that I commune with them quite well.

Dean: [Huffing a chuckle] Yeah, no kidding. I don’t think I can ever forget when you…uh…showed up covered in ‘em.

Castiel: You do realize that I was not at all in my right state of mind when that occurred, correct?

Dean: [Turning slightly red] Y-yeah, but…doesn’t matter, that image will be seared into my brain forever. [Quickly redirecting the conversation] Can’t believe you didn’t get stung…

Castiel: As I said, I commune with bees easily. I needn’t fear being stung by them.

Dean: So, you love bees, plain and simple, but what about me?

Castiel: I don’t recall you ever saying what your favorite animal is…you don’t have a particular affinity for animals as a whole.

Dean: I never really gave it much thought, but man, I gotta say that tigers are cool.

Castiel: [Surprised] Really? I was under the impression that you disliked cats due to your allergy towards them.

Dean: Little cats who leave hair everywhere? Yeah, not my thing. But giant roaring _tigers_? They’re just about the most badass thing out there.

Castiel: [Bowing his head in acknowledgement] Fair enough.


	15. Question #14: What is your best friend’s favorite color?

Castiel: From what I have observed, you are drawn to dark colors.

Dean: You’re on the right track. Make a guess!

Castiel: [Carefully considering] You…own many items of the color black, such as your car…by any chance would black be your favorite?

Dean: You’re right on the money. I’m startin’ to think you might know me too well for my own good…and you, on the other hand, seem to like light-colored things. So…pfft, I dunno, do you like white?

Castiel: That is correct, Dean. White is my favorite of the colors.

Dean: [Surprised that he actually got it right with his offhanded guess] Wait, seriously? Maybe _I_ know _you_ too well for your own good.

Castiel: White may be plain, but it reminds me of home. It is the predominant color of heaven, where I spent much of my life. [Something else occurs to him] But…green is definitely another favorite color of mine, since it is so closely tied to the natural beauty of earth…

[Castiel stares into Dean’s green eyes for a few tense moments, and Dean clears his throat and hurriedly turns back to the list, hiding his blushing face behind it]

**Notes for the Chapter:**

> Dean loves the color black. That means he's gunna love Castiel's wings, amirite? ( ͡° ͜ʖ ͡°)


	16. Question #15: What is your best friend’s favorite movie?

Dean: If you don’t get this right, I am going to be so disappointed in you.

Castiel: You won’t be disappointed, then. You forced me to sit down and watch it with you. The…Shining, right?

Dean: [Grinning proudly at Castiel] With my man Jack, yeah! You got it!

Castiel: I can see why you enjoy that film as much as you do. It has many supernatural elements relevant to your life, and you are rather enthused by…your man Jack’s performance.

Dean: And it shouldn’t be too hard to figure out your favorite movie; unless you’ve been going off watching movies without me.

Castiel: Only the occasional nature documentary on Netflix.

Dean: Good, this should be a cinch, then. Out of all the movies I’ve made you watch, Star Wars was your favorite, right?

Castiel: Is that the one with the colorful blades made of light?

Dean: That’s the one! It was kinda hard to tell, but that was the one you looked the most invested in.

Castiel: I did greatly enjoy that movie…out of all the movies I have seen thus far, it was my favorite. A thoughtful illustration of humanity’s struggles against oppressive force…

Dean: We gotta show you the rest of the trilogy, man. You, me, and Sammy are havin’ a movie marathon sometime this week, and that’s non-negotiable.


	17. Question #16: What’s your best friend’s favorite food?

Castiel: Pie.

Dean: Burgers.

Castiel: …That one was…awfully easy to answer.

Dean: If you’re lookin’ for more of a challenge, you can try to guess my favorite type of pie.

Castiel: Alright… [Brows furrowing in concentration] Um…you seem fond of…but you also have professed your taste for…oh, but there’s also- no, wait you have also said that you enjoy-

Dean: [Resigned] Don’t hurt yourself. I actually can’t choose a favorite; they’re all _so damn good_.


	18. Question #17: What is a weird food that your best friend likes?

Dean: Okay, I held my tongue about this for a long time, but…dude, what’s with the honey?

Castiel: The…honey?

Dean: Yeah, the honey! I swear you’re going through a phase where you put it on literally everything we put in front of you!

Castiel: Honey acts as a sweetener. It has been difficult for me to enjoy taste the same way since my exposure to the sense as a human, but honey makes it easier to distinguish the food molecules and assign them meaningful flavors.

Dean: And that’s fine, but…honey on _french fries_?

Castiel: [Getting defensive] It’s not near as outlandish as it sounds.

Dean: Honey in _tomato soup_?

Castiel: That’s not actually uncommon, I looked it up on the Google-

Dean: Honey in your friggin’ _orange juice_?!

Castiel: I simply enjoy honey to an abnormal degree!

[Neither say anything for a few moments as the petty conflict settles.]

Castiel: Besides, with some of the unholy amalgamations of food you have crafted over the years I’ve known you, you are in no position to criticize me.

Dean: “Unholy…?” I’ll have you know, my food combinations are works of art.

Castiel: Dean. I have personally witnessed you placing a whole slice of pizza in between the buns of a hamburger and dipping it into microwaved cheese sauce.

Dean: …Please don’t tell Sam.

Castiel: Too late. He is already secretly planning a dietary regime that he will enforce on you upon its completion.


	19. Question #18: Have you ever taken a trip together?

Castiel: Dean and I collaborate on hunting cases across the United States, although Sam is normally along with us.

Dean: Yeah, I don’t think you and I have run a solo case since…Waterville, when we trapped Raphael. Back when… [Snickers] Back when you met Chastity.

Castiel: [Rolls his eyes] We should take a trip sometime… _without_ any mentions of Chastity.

Dean: I dunno, man. I don’t drop inside jokes so easily. [Turning more serious] But you’re right, we should take a trip, just you and me. Might not even need a case; it’d just be an excuse to get out and about for once without any otherworldly baddie summoning us.


	20. Question #19: What’s your best friend’s favorite TV show?

[Dean looks at Castiel expectantly. Castiel sighs.]

Castiel: Above all other television shows in existence, Dean loves Dr. Sexy M.D. most of all.

Dean: And you and I are gonna sit down and marathon it one of these days, I swear on my grave.

Castiel: You mean the grave that you crawled out of when I rebuilt your body so that it could rehouse your purified soul?

Dean: [A little put off by that memory] Uh, yeah, sure, that grave…

Castiel: I will be genuinely surprised if you can guess my favorite television series. And yes, I do have one.

Dean: It’s Sherlock.

Castiel: [Momentarily speechless] How…did you…?

Dean: I may have looked through your Netflix watch history…just for curiosity’s sake. You should get Sam to watch it too; it’s plenty nerdy enough for the both of you.


	21. Question #20: What is the name of your best friend’s first crush?

Castiel: I don’t understand. Why would someone ask what the first thing you crushed was? Is it commonplace for humans to have a significant first item that they squash?

Dean: [Chuckling under his breath, but growing nervous] Uh, no, Cas. A crush is…someone you like. Romantically.

Castiel: [Slowly understanding] Oh, that makes more sense…well, I can’t say that I’ve known you long enough to say with any confidence who your first romantic interest was. Some of your most significant “crushes” since I’ve known you include Lisa Braeden, Dr. Sexy M.D.-

Dean: [Rushing to stop him] H-hold on, that’s fine Cas! My, uh, first crush is the only thing being asked about here…

Castiel: [Surrendering] That’s…true. Who was your first crush then, Dean?

Dean: Definitely Daphne from Scooby Doo. Used to watch that all the time when I was a kid. [Quirking an eyebrow and looking pointedly at Castiel] And you?

Castiel: [Suddenly looking extremely nervous and unable to meet Dean’s inquisitive gaze] Um…I…

Dean: Wait, don’t tell me! I can totally figure it out! You said yourself that you’d never had any occasion for “cloud seeding,” so it wouldn’t have been until after you left heaven, right?

Castiel: [Still immensely nervous] That…is correct, yes.

Dean: Alright, think I’ve got it, then. It has to be Meg.

Castiel: [Hurriedly looks back up to meet Dean’s questioning gaze] M-Meg? Oh, right…yes, it was...Meg was definitely…definitely the…first.

[Something bordering on disappointment flashes over Dean’s face, but he reels it in rather quickly and returns to the list.]


	22. Question #21: Which three things would your best friend take with them on a deserted island?

Dean: First things first, Cas would need his phone. God knows he can’t go a single day without sending me or Sam a string of emoticons for no reason at all.

Castiel: I would like to think that my use of emoticons does have meaning. That’s the way I intend it.

Dean: What about the time you sent me the poop emoji fifty-seven times in a row?

Castiel: …I was upset when I returned to the bunker and found neither you nor your brother within it.

Dean: So when you send the poop emoji, it’s ‘cause you’re pissy. Noted. Now, other than your phone...you’d probably want a supply of honey, since you practically live off the stuff. Add a beehive- or a beekeeping box or whatever- to your list.

Castiel: [Staring into space as he pictures this] Tending to bees would be a nice way to pass the time while I awaited rescue.

Dean: Other than that…a book. ‘Cause you’re a nerdy lil’ dork. [Crossing his arms] Beat that!

Castiel: In a hypothetical scenario where you are trapped on a deserted island, I would rest at nothing to ensure that you were safely brought back. But for the time until I would be able to retrieve you…I suspect you would enjoy having a supply of various pies…

Dean: Mmm…yeah…

Castiel: A cellar of beer…

Dean: Sounds good to me…

Castiel: And your brother for company.

Dean: Hell, this sounds like it could be a full-on island vacation! Boy do Sam and I need one of those…

Castiel: That could be arranged.

Dean: Not ‘til we get a break from all the insanity that is our lives. There’ll be a chance one of these days, and you’d better believe I’m gonna take it. [Pointing at Castiel] You’re invited too, of course.

Castiel: [Smiling warmly at the thought] I would greatly enjoy a trip to an island alongside you and Sam.


	23. Question #22: Who is your best friend’s celebrity crush?

Dean: Crush? Singular? As in we can only have one? [Scoffs] Well, Cas, you’ve got a pool to choose from.

Castiel: [Hesitant] I…know next to nothing about most modern celebrities. I’m not confident that I can provide an answer.

Dean: Take a wild guess. Anything that comes to mind.

Castiel: [Deep in thought] I suppose…you do act rather infatuated towards Dr. Sexy, and by extension the actor who plays him.

Dean: [Blushing] Um, wh-what? No, man, no, that’s not…uh, what about you? If you’ve got the hots for any celebrities out there, I wouldn’t know it.

Castiel: I don’t, truly. I have hardly given any thought to celebrities in general.

Dean: Even Princess Leia? C’mon man, I saw how you looked at her when we were watching A New Hope.

Castiel: Although she was…pretty…I did not feel any attraction towards her or her actress, romantic or otherwise.

Dean: …Damn, you are probably the only person I’ve ever met who literally doesn’t have a celebrity crush. We’ll see what we can do about that.


	24. Question #23: What’s a thing that you have never told anyone else, including your best friend?

Dean: Oh, c’mon. This is just a cheap shot to try and get a secret out of us.

Castiel: Not necessarily. I think it’s a good exercise in building trust.

Dean: You go first, then. I’m not exactly a share-and-care kinda guy.

Castiel: Very well…I have not confided this in anyone, but as my best friend, I trust you more than enough to share it. Simply put, there isn’t a day that goes by in which I don’t pray to my father at least once. He never answers, but…it’s comforting all the same.

Dean: [Not entirely sure how to address the downer of a subject] That, uh…that’s pretty heavy. [Chuckles nervously] I’m sorry he doesn’t answer, Cas, really. I know what that’s like…

Castiel: [Smiling appreciatively at Dean’s understanding] And what about you? Whatever secret you plan to divulge, I promise I will keep it to myself and reserve judgement towards it.

Dean: Like I said, I’m not exactly a share-and-care type of guy, but… [He briefly considers a few things he could answer with, cringing at some points] Ooh! How about this: so one time, Sammy and I were on a case, a simple salt and burn somewhere out in Idaho…we split up to look for clues, and I ended up getting the motel room to myself. I took Sam’s laptop and uh… [Coughs] went to a website I probably shouldn’t have. Ended up getting this nasty virus on his computer. Couldn’t figure out how to get rid of it, so I just panicked, erased the evidence, and left it like that. Even with all his computer smarts, Sam couldn’t for the life of him figure out how to fix it. Ended up having to reformat the whole thing. He was _pissed_. But, to this day, he still hasn’t pinned it on me.

Castiel: [Has been listening attentively] Have you ever considered telling him the truth?

Dean: Hell no! I wasn’t sharing this to get it off my chest or anything, if that’s what you’re thinking. Looking back on it is hilarious. Just figured it’d be more fun to have someone else to laugh about it with.

Castiel: In all honesty… [Cracks a grin] I can see the humor in it, even if it is at Sam’s expense.


	25. Question #24: What do you admire most about the other person?

Castiel: You have many admirable traits, Dean, but if I were to choose one…

Dean: Oh, god. Chick-flick moment incoming.

Castiel: I greatly admire your ability to genuinely, deeply care for the people around you, even total strangers. You have saved so many people through your efforts as a hunter, and you are wholly devoted to protecting the people you care about. That…is a wonderful trait to have.

Dean: [Flushing under Castiel’s praise] Jeez, man, just, uh…just doin’ my job. [Regaining some poise] Now, uh, you…you’re one hell of a steadfast friend. Since you rebelled against heaven, your loyalty’s been here with us, and everyone knows it. Well, ‘cept for that time you were working with Crowley, but…even then, you were still doing that…uh, for me.

Castiel: [Quietly] I would prefer to not recall that particular series of events.

Dean: You and me both…but yeah, you’re always so reliable. Like, no matter how many times you stray or get taken away, you always come back. I know I can trust you, and even if you do screw up, so what? Everyone else does too! At least you screw up trying to do the right thing. [Momentarily struggles with something] You…deserve…better than what you usually end up getting, Cas. You’re a good friend. Really, I mean that, chick-flick moment or not.

Castiel: [Deeply touched by Dean’s words] That means an awful lot coming from you, Dean.

Dean: [Hiding a blush] Y-yeah, don’t mention it…


	26. Question #25: What does your best friend always carry around wherever they go?

Dean: Just gonna say it now: trench coat.

Castiel: Does my trench coat count, Dean? Technically I do not “carry” it so much as wear it everywhere I go.

Dean: Nope, still totally counts. It’s basically iconic to your identity, it’s a big deal.

Castiel: If you are certain…as for your own ever-present belongings, I have never once seen you without the keys to the Impala on your person.

Dean: [Reaches into his pocket and presents the keys in question] Gotta keep Baby close at all times!

Castiel: Does your infatuation with your car count as another “crush?”

Dean: Nah.

[Dean proceeds to literally kiss his keys while Castiel watches, wondering why humans have to be so weird.]


	27. Question #26: What was your best friend’s favorite TV show as a kid?

Castiel: I’m just guessing, but since you mentioned this show earlier… “Scoo Doo?”

Dean: Scooby Doo, Cas. And yes, it was my favorite for a long time. Used to imagine goin’ on spooky investigations with Mystery Inc. all the time. Funny how that actually ended up kinda coming true…minus unmasking the monster as a person in a costume at the end. I wish that’s how our job worked, actually. Things would end with a lot less bloodshed.

Castiel: I wish I could provide an answer to this question, but since I was created in heaven and there were no televisions or shows in existence when I was a fledgling, I have nothing to respond with.

Dean: Wait, baby angels are actually called fledglings?

Castiel: When we are first created, yes. We do not “age” in the same way that humans do, and our mental faculties are well beyond that of a newborn human, but we still must be guided and taught by our elder siblings.

Dean: Doesn’t sound too bad…well, except for not having cable.


	28. Question #27: Who would play your friend in a movie?

[Dean starts laughing to himself shortly after he reads the question.]

Castiel: What? What’s funny?

Dean: I dunno I just… [Lets out a string of chuckles] Out of friggin’ _nowhere_ I got this mental image of Leonardo DiCaprio wearing your trench coat and tie, and I… [Laughs a little more]

Castiel: …Perhaps this would be more humorous to me if I actually knew who that was.

Dean: [Between more laughs] Yeah, yeah it would be!

Castiel: Unfortunately, this is yet another question I cannot answer. I’m not at all familiar with actors, and I haven’t seen any who look anything like you. You could always just play yourself.

Dean: [Having finally clamped down on his laughter] Oh, I don’t know about that. I’m not much of an actor. I already played myself once in an alternate universe, and that did _not_ go well.

Castiel: Hmm…have you settled on someone who could play me?

Dean: I’m tryin’, but…[Snorts] All I can think of right now is Leonardo DiCaprio trying to speak in your voice! [Resumes his laughter]

Castiel: …So this Leonardo would play me in a movie. I’m not sure who he is, but I trust your judgement.


	29. Question #28: What phobias does your best friend have?

Castiel: Dean has a severe fear of flying in airplanes.

Dean: ‘Cause planes crash!

Castiel: _Sometimes_ they crash, Dean. Most of the time, they do not.

Dean: [Grumbling quietly] Doesn’t stop me from being freaked out by ‘em.

Castiel: Your fear of flying may be unfounded, but I don’t aim to invalidate it. Perhaps it seems odd to me because I am a winged creature and flying comes so naturally to me.

Dean: A winged creature who doesn’t seem to be afraid of, like, anything. Seriously, dude, what does it take to freak you out? You’re either constantly stoic or chill all the time.

Castiel: I may not show it, but I do have fears.

Dean: The only fear I’ve seen from you is a fear of getting laid. Well…until… _April_. [He spits out the name with open disgust]

Castiel: I don’t like recalling April. My memories of her reek with…regret.

Dean: As they should. She totally used you. But enough about her! Your phobia is of getting laid, and that’s that.

Castiel: [Turning sheepish] I wouldn’t say I have a phobia, per se…

Dean: Well, you’re afraid of some part of it. Which is fine! Your choice whether to do it or not anyways. I’ve got your back either way.

[Something about that makes Castiel turn even more sheepish, and for once he’s the one eager to move on.]


	30. Question #29: What are you obsessed with?

Castiel: Outside of hunting, our interests are quite different. I prefer nature while you prefer mechanical devices.

Dean: You just _like_ nature, though. When it comes to obsessions, like I said earlier, you’re addicted to honey at this point.

Castiel: I find my obsession with honey to be no stranger than your obsession with pie and greasy diner food. Or your obsession with your car. Or your obsession with classic rock. Or your-

Dean: Alright, I get it, I have a lot of obsessions. What can I say? I’ve got a passionate personality.


	31. Question #30: If you friend has a nickname or many nicknames, what are they?

Dean: Pretty much everyone calls you Cas now. [Smirking proudly] I’m the one who started that.

Castiel: I enjoy that shortening of my name. It has helped me to differentiate my identity since rebelling against heaven. I don’t believe I ever thanked you for my name, Dean.

Dean: No need! I’m great at nicknames; just ask Sammy.

Castiel: Your name would be challenging to shorten, seeing as it is only comprised of four letters. You have been known as “The Righteous Man” in the past.

Dean: [Scoffs] Yeah, right. There was hardly ever anything righteous about me.

Castiel: And Crowley enjoys calling you “Squirrel,” though I don’t understand why. I’m assuming it’s either another cultural reference that I don’t understand…or just a stupid demon being stupid and confusing.

Dean: Man, you really hold a grudge against Crowley don’t yo-

Castiel: _Yes._


	32. Question #31: What is something weird that your best friend likes?

Castiel: In general, Dean’s interests are within the norm expected of humanity…save for those related to his hunting, I suppose. He does have a somewhat morbid interest in weaponry, although that is mostly out of necessity for his job.

Dean: You, on the other hand, have this weird sense of… “wavelengths” and “spheres” that you keep talking about. I have never understood what you mean when you bring that up.

Castiel: That is hardly considered weird among angels. It is part of our way of perceiving and processing the world, just as humans do through their senses.

Dean: It sounds like a lotta crazy to me, but hey, I guess I’m not meant to understand.


	33. Question #32: What’s a thing your friend doesn’t know about you (yet)?

Dean: Great, now we gotta spill _more_ secrets?

Castiel: Think of it as another trust-building exercise, Dean. I am more than willing to share more about myself so long as you are too.

Dean: Okay, well, I gotta think…what _don’t_ you know about me yet…?

Castiel: There is little I don’t know about you, seeing as I physically rebuilt your body molecule by molecule when I rescued you from Hell.

Dean: [Blatantly ignoring Castiel’s statement] You go ahead and tell me something about yourself, I’ll…I’ll think on mine for a bit.

Castiel: Very well. [Getting a bit nervous] I…I have been thinking about what you have said regarding my “phobia” of physical intimacy…and it’s come to my attention that I should clarify: I am not afraid of it, I simply do not desire it.

Dean: [Caught off-guard by Castiel being this open] Oh, uh…

Castiel: At least not in the traditional sense. I suppose that I am capable of attraction, just…not outside of the context of an established emotional bond.

Dean: [Takes him a while to formulate a response, but he’s careful when he does so] I…think there’s a word for that. Can’t remember it, but I bet Sam would know.

Castiel: I am aware. I have briefly researched this…I believe the word is “demisexual?”

Dean: Yeah, that’s it! I kept thinking “demonsexual” but I knew that couldn’t possibly be right… [Pauses] Dude, did you just come out to me?

Castiel: I…believe I did.

Dean: …Cool.

Castiel: So this doesn’t strike you as odd, in any way?

Dean: Course not! Just means your type is…uh, people you know. Makes sense to me.

Castiel: That is a relief. Thank you, Dean.

Dean: No worries…incidentally, you’ve given me inspiration for what I can tell you.

Castiel: [Something hopeful flickers in Castiel’s expression] Oh? I am here to listen.

Dean: Yeah, you told me your type, so I’ll tell you mine! Dunno why, but I always liked dark hair best.

[Dean shrugs while Castiel faintly cocks his head. Slowly, realization settles onto Dean’s face as his eyes flick up to Castiel’s own dark hair.]

Dean: [Rushing to correct himself] Uh, _long_ and _wavy_ dark hair, that’s my type. In case you ever wanna…hook me up with someone…heh…

Castiel: [His glimmer of hope has been swiftly extinguished] I…see. I will keep this information on hand in case it is needed.

**Notes for the Chapter:**

> Demi!Castiel has always been my headcanon. To me, it just suits him. UwU


	34. Question #33: Is there anything you don’t like to do together?

Dean: I think we both mutually agreed that getting stuck with dishwashing duty is the worst.

Castiel: It is among the least pleasant of routine activities here in the bunker. I’m not sure what it is about wet food particles, but… [His face scrunches up somewhat] My vessel cringes with revulsion each time I come into contact with them.

Dean: It’s not that the food grosses me out like Cas here, but it’s just _tedious_ and we usually end up with a bigger mess than we started with. Our kitchen sink really needs some new plumbing; it takes forever to get everything down the drain.

Sam: [From another room off camera] Are you guys complaining about basic chores again?

Dean: [Shouting back over his shoulder] Nah, Sammy, just earning ourselves some free pie!


	35. Question #34: What is your friend’s worst habit?

Castiel: You mean other than constantly putting himself in danger and dying as a result?

Dean: [Under his breath] Yeah, like you’re one to talk…

Castiel: Dean does have an unsavory habit of chewing with his mouth partially open. And even when his mouth is closed, he chews unnecessarily loudly.

Dean: It’s food, man, I’m just tryin’ to enjoy it!

Castiel: At the expense of what little appetite I can manage to work up as an angel.

Dean: Hey, no one’s forcing you to eat around me. But, uh, I’ll work on it, alright? I hardly even think about table etiquette anymore…

Castiel: I would appreciate that, Dean. Bad habits aside, I do enjoy your company while eating.

Dean: Speaking of which…your only bad habit that I can think of is your whole “disregard of personal space” thing. You’ve gotten a lot better about that over the years but…sometimes it still shows.

Castiel: …I had nearly forgotten about that. [Scoots his chair back from Dean’s somewhat]


	36. Question #35: If your friend met a genie and was granted a wish, what would it be?

Castiel: Dean was once captured by a Djinn, so this has technically already happened. His wish, although it was granted against his will or awareness, was for his mother to have never died. I’m assuming that if he encountered another, friendlier genie, he would make the same request.

Dean: [A little shocked at this being brought up] …How’d…you…know about that? I don’t think I ever told you that story.

Castiel: You aren’t the only person with stories to share, Dean. Sam enjoys exchanging stories of past hunts with me on occasion too.

Dean: …That sly dog. Please tell me he didn’t-

Castiel: Yes, he did tell me of the time when you were infected with ghost sickness and screamed at a cat, as well as the case in which your mentality was changed to that of a dog’s. And he said something about you “getting wailed on by Paris Hilton,” whatever that means-

Dean: [Forcefully cutting him off] Alright, enough! I get it, Sam loves to share embarrassing stories about me with my friends behind my back. Let’s get back to the question.

Castiel: …As you wish.

Dean: Now, if you could make a wish on a genie without the whole bloodsucking coma side of it…and since you were serious with mine, I’ll be serious with yours too…you’d probably want your dad to be around, right?

Castiel: …I was going to say that I would wish to undo all the damage I have done on heaven and earth to redeem myself, but that’s certainly another consideration.

Dean: Close enough!


	37. Question #36: What does your friend’s ideal birthday party look like?

Dean: …Have you ever even had a birthday party?

Castiel: No, Dean. I don’t even know when my birthday is.

Dean: …Remind me to pick a date so we can throw you one, then. I bet you’d like to have it outside, like a picnic or something. And Sam and I could show you all the human birthday traditions, and I bet I could find a way to bake a cake with honey somehow-

Castiel: It’s a nice thought, but you don’t _have_ to do all of that for me, Dean-

Dean: To hell with that, I wanna throw you a party! It’s been a long time since a birthday’s been properly celebrated around here!

Castiel: …That is true. I recall you spend your birthdays either touring the bars around wherever you happen to be, or simply doing as you please at home all day. Sam gives you some presents, but you should have a proper party as well.

Dean: I won’t object to that; long as there’s pie and beer aplenty!

Castiel: [Grinning] That’s how I figured you would like your party to be.


	38. Question #37: What’s your favorite thing to do together?

Castiel: There are many things we enjoy doing together…

Dean: Having you along on a hunt is always fun. Kinda stressful since it’s one more person to keep track of and worry about, but hey, that’s the hunting life.

Castiel: We have a lot of fun watching movies together when the opportunity arises.

Dean: Yeah, those are good times…when there’s no monster around calling us out to the field, and we can just do the stuff that normal friends do for once.

Castiel: Yes, staying close together and indulging in mindless television is a nice break from the chaotic ramifications of our lives.

Dean: [Looks sternly at the camera] He…means…staying close as in sitting beside each other. And not anything else.

[Castiel looks puzzled by Dean’s need to clarify, but he doesn’t speak up.]


	39. Question #38: If you were ordering a pizza for your best friend, which toppings would they want?

Castiel: …Dean, is it acceptable to put-

Dean: Honey on pizza? [Sighs] Yeah, go nuts. Is that all you’d want?

Castiel: I’m not averse to experimenting with other toppings, but honey is a must.

Dean: Then you might like beef on pizza too, since you love burgers so much…dunno how well that’d go with honey, but you’d probably eat it anyways.

Castiel: That sounds delightful. If I were to guess…I would order you a pizza with pepperoni, as that seems to be a staple of pizza variety and I’ve seen you eating it before.

Dean: [Chuckling] Since when have you seen me eating a-

Castiel: When you constructed that monstrosity of pizza, hamburger, and cheese sauce.

Dean: …Oh, right. You’re never gonna let that go, are you?

Castiel: Neither is Sam.


	40. Question #39: What’s your friend’s favorite food?

Castiel: Pie.

Dean: Burgers.

Castiel: …I feel like we’ve answered this question already.

Dean: [Flipping back through the list] Yeah, we did! This question’s printed on here twice! [Shaking his head] That’s just poor craftsmanship.

Castiel: I’m sure it was an honest mistake, Dean.

Dean: Yeah, whatever. Next.


	41. Question #40: What’s your friend’s favorite ice cream flavor?

Dean: Wait a minute…dude. You’ve never had ice cream before, have you?

Castiel: I’ve never had occasion to try it.

Dean: … _This is an injustice that must be undone._

Castiel: Ice cream is considered a dessert, is it not? So that buffet may very well have some for me to try.

Dean: Perfect! Oh man, I cannot _wait_ to see your face the first time you try it.

Castiel: Which flavor do you think I would like best, Dean?

Dean: Probably honey flavor, if that’s a thing. Out of the more common flavors, though, I could see you being a vanilla man.

Castiel: I would venture a guess of your favorite flavor, but I am not familiar with different varieties of ice cream…

Dean: Just for future reference, in case you’re ever in a situation where you need to get me ice cream, remember two words: Cookie. Dough. Anything with cookie dough in it is good enough for me.


	42. Question #41: What does your friend do on a free day?

Castiel: Dean enjoys cooking sometimes when he is at leisure to do so, and otherwise he works on the various vehicles in the bunker’s garage and forcibly ropes me, Sam, or both of us into playing board games with him.

Dean: C’mon, you loved Monopoly night!

Castiel: [Fixes Dean with an intense stare] That night will forever live in infamy as the night that nearly tore our team apart. Sam _trusted_ you to let him stay on your Boardwalk for free just that once, just until he could save up the necessary funds to pay rent, and you tossed away his trust with hardly a second thought. I have never seen such a look of sheer betrayal on his face as in that moment.

Dean: Them’s the rules, Cas. It’s a dog-eat-dog world when it comes to Monopoly.

Castiel: [Crossing his arms] You still shouldn’t have forced me to hand over my monopoly of railroads as payment when I couldn’t afford your rent.

Dean: [Laughing victoriously to himself for a moment] When he’s not getting his ass kicked at board games, Cas is usually glued to Netflix on our free days.

Castiel: …How…would I glue myself to a video streaming service? It’s not a physical thing, that doesn’t make any-

Dean: You’re taking things literally again, Cas. Don’t worry about it.


	43. Question #42: What is your best friend really good at?

Dean: Speaking of Monopoly, Cas here’s got the monopoly on smiting things. One touch and boom, you’re dead.

Castiel: The skill of smiting is far from monopolized. Other angels can kill beings through the same methods as I do, and you and Sam are very talented at dispatching evil forces as well.

Dean: Yeah, well, you’re awesome at it anyways. What about me, huh?

Castiel: You are an exemplary hunter, and as I mentioned earlier, you are very skilled at repairing and working with cars and other mechanical matters.

Dean: _And_ I’m a champion pie eater.

Castiel: Right, you are also a champion at consuming copious amounts of pie, at least within our team.


	44. Question #43: What is your best friend terrible at?

Dean: No offense, Cas, but you really need to work on your interrogating skills.

Castiel: How do you mean?

Dean: As in, don’t shout at emotionally unstable interviewees and accuse them of murder. Oh, and don’t waste your time interrogating cats.

Castiel: I’d nearly cracked that feline…

Dean: Just…work on your social skills in general. I get that you’re gonna be socially awkward one way or another, but we gotta train you better so you can help us more on cases.

Castiel: I’ll try, Dean. Although I’m not the only one who struggles through social blunders.

Dean: …Surely you’re not talking about me, right?

Castiel: Although you can be very charismatic and socially capable in most circumstances, I’ve heard that you struggle with on-the-spot comebacks.

Dean: Yeah, well you…struggle with…on-the-spot comebacks…

Castiel: …You have only served to prove my point. We can work on improving our social shortcomings together, Dean. There is no shame in it.


	45. Question #44: Have you two ever had a fight? Why?

**Notes for the Chapter:**

> There some mild angst ahead so be warned my friends ;w;

[Both glance nervously at each other after reading the question. Neither seems eager to discuss this topic.]

Dean: [Coughs into his fist] We, uh, we’ve had our fair share of conflicts, yeah…

Castiel: Such as when I directly deceived you and worked with Crowley behind your back.

Dean: Yeah, that…that one was really bad. Probably our worst, actually.

Castiel: There was also the span of time following my state of lunacy after I took Sam’s memories from Hell as my own. You were not…particularly happy with me during that time…and after what I’d done and my reluctance to participate in righting it, I don’t blame you.

Dean: That one sucked too, but we resolved it, right? Turned out for the best?

Castiel: [Smiling fondly] “I’d rather have you, cursed or not?”

Dean: [Flushing and looking away] Yeah, right, I remember that… 

Castiel: And then there was… [Face falls enormously] When…you had the Mark of Cain, and…

Dean: [Rushing to make Castiel feel better] W-we don’t have to talk about that one! That one…oh, that one was…bad…I _hated_ that one, I… [Shakes head determinedly] No, let’s…leave that one alone, alright buddy?

Castiel: [Managing a grateful smile] Thank you, Dean.


	46. Question #45: When is your friend’s birthday?

Castiel: Dean’s birthday is January 24th, 1979.

Dean: Well look at you, Mr. Calendar. But like you pointed out, you don’t exactly have a birthday, or at least not one that we can figure out.

Castiel: I cannot recall when I was created, or even if the concept of dates existed at the time.

Dean: Well let’s get you a birthday, then! What day do you wanna have for your birthday? It can be whichever one you want.

Castiel: Hmm…when I think back to significant dates in my life, the one when I took a vessel and met you on earth stands out. It served to shape my destiny in ways I couldn’t have possibly imagined at the time, and in a sense I was “reborn” on that day.

Dean: What day was that? September…18th, was it?

Castiel: I believe so.

Dean: So it’s settled! September 18th is your birthday! Oh man, I gotta get started with planning how to celebrate it…

Castiel: Dean, it’s only February. My birthday won’t be for months.

Dean: Shhh, I’m party planning.


	47. Question #46: Does your friend have an expression or phrase that they say very often?

Castiel: Dean does have a certain phrase that he repeats regularly…although it could be considered rude by some.

Dean: It is not! C’mon, dude, say it. I didn’t know how badly I wanted to hear you say it until now, _please_.

Castiel: [Sighs tiredly] Son…of a bitch.

Dean: [Giggles like a ten-year-old]

Castiel: I hope that brought you satisfaction.

Dean: You have no idea. Here, I’ll even say your token catchphrase back to you to make it even. [Clears throat and attempts to speak in Castiel’s voice] I don’t understand that reference.

Castiel: I don’t sound like that.

Dean: I’ve got more! [Resumes talking like Castiel] Hello, Dean. I’m the one who gripped you tight and raised you from perdition.

Castiel: You’ve made your point. Let’s move on.

[Dean continues laughing to himself.]


	48. Question #47: Where was your best friend born and where would they like to live?

Dean: You were born- er, created in Heaven, right?

Castiel: [Nods his head] That is correct, Dean.

Dean: And you’d wanna live… [Hopeful] Right here in the bunker?

Castiel: I am content to inhabit the bunker, yes. But if it weren’t for the bunker, I would enjoy living in the Netherlands. Their landscapes are my favorite out of all those I’ve seen in my earthly travels.

Dean: …Well now I can’t help but picture you wearing wooden clogs.

Castiel: And you were born in Lawrence, Kansas. I’ve heard you say on more than one occasion that you’re happy to be living here in the bunker.

Dean: Sure am. [Takes a moment to look around and admire his home]


	49. Question #48: Who was the last person your friend kissed?

Castiel: [Goes red] Why…would a question like this be on here?

Dean: ‘Cause people love to pry. You don’t do much kissing, least not that I’ve seen, but last person I know for sure you probably kissed was… [Cringes a little, but tries to hide it] April, right?

Castiel: Actually… [Sighs to himself] It was Hannah.

Dean: [Does a double-take] Hannah? As in, your fellow angel and _sister_ Hannah?

Castiel: It was complicated. Her vessel’s husband tracked us down during our travels, and we had to keep up a ruse to force him off our trail…I can’t speak for Hannah, but it involved a rather large amount of discomfort on my part.

Dean: …Freud would have a field day with your family, you know that, right?

Castiel: Perhaps…you’re in much the opposite situation as me. To my understanding, you kiss people rather frequently. I’m not certain I can pinpoint the last person you kissed…

Dean: Yeah, me neither. Can’t remember, stuff gets jumbled around up here when you’ve been at this for as long as me. I’m practically an expert when it comes to all things kissing, ya know. [Flashes a smirk]

Castiel: [Goes red again and glances away] I wouldn’t doubt it.


	50. Question #49: As a kid, what did your best friend want to become when they grew up?

Castiel: I know that you surely didn’t aspire to be a hunter from your youngest years, but since I didn’t know you during that time, I honestly have no clue what you wished to become.

Dean: Actually, I’d nearly forgotten…haven’t thought about that in a long time. I used to want to be a firefighter, even for a while after my dad got into hunting.

Castiel: [Regards Dean sympathetically] Was that because of the nature of your mother’s death?

Dean: What? No, no, I wanted to be a firefighter even before she died…

Castiel: Oh…I am sorry to bring it up, then.

Dean: No worries…for a while I also wanted to be a Rockstar, but of course _that_ didn’t pan out. Did you uh, even get to have aspirations for your future as an angel?

Castiel: We simply took on the roles expected of us, but aspirations weren’t forbidden.

Dean: So didja actually want to be part of the garrison? Or is that just what heaven commanded?

Castiel: [Faintly smiles at the memory] I did want to join the garrison, even as a fledgling. It was all planned out for me, though, and I never considered that I could have other options at the time.

Dean: Which, knowing how freakin’ bureaucratic heaven is, wouldn’t have done any good anyways.

Castiel: Yes…later when humankind had progressed, I found myself longing to walk among them and help guide them however I could. I could ease their earthly worries and pains…I suppose that’s what I’m doing now with hunting. It seemed such a far-off dream back then.

Dean: …Sometimes I forget just how old you really are.

Castiel: It’s all relative, Dean. Even with my age, I am still constantly learning and growing as an individual thousands of years later. You have done much to help me and guide me towards fulfilling that long-buried dream.

Dean: …Do I say “you’re welcome?”

Castiel: My gratitude was implied, so yes, that would be appropriate.


	51. Question #50: What is a unique thing about your friend that only a few people know?

Dean: [Smirks and looks directly into the camera] Well, in case you didn’t pick up on it yet, Castiel here is an angel. And I’m not just saying that as a compliment, I mean he’s _literally_ an angel. Straight from heaven with wings, halo, and all.

Castiel: Actually, angels do not have halos. That is a myth perpetuated by centuries of misinformation.

Dean: Aw, no harps either?

Castiel: [Ignoring Dean for the moment] Relatively few people are aware that although you are now for all intents and purposes human, you were briefly a demon.

Dean: [Proudly] Knight of Hell, actually.

Castiel: That is hardly anything to be proud of.

Dean: Yeah, well, being a demon sucked, but if you’re gonna be one you may as well be one of the badass ones.


	52. Question #51: If your best friend is single, describe their dream partner.

[Castiel shifts uneasily after he reads the question.]

Dean: [Notices immediately] …What?

Castiel: Nothing, I’m just…

Dean: …Oooooh, I get it. [Momentarily waggles eyebrows] You’ve got a crush that you’re scared I’m gonna figure out.

Castiel: [Looking in practically the opposite direction] You could…say that…

Dean: Let’s see what I piece together, then…for starters, your dream partner would have to be someone you know pretty well, right?

Castiel: [Still visibly uneasy] That’s how it works, yes.

Dean: Hmm…and judging by your past interests, you mostly seem to be into other supernatural entities…then again, there was Nora…and hair colors have ranged from brunette to nearly blonde… _man_ , you are tough to pin down.

Castiel: That may be because physical appearance doesn’t play nearly as large a role for me as the appearance of one’s soul does.

Dean: …Well, great, I have no idea how to figure out your type, then. So in short, you dream partner is someone you know who has an attractive soul, whatever that looks like. Your secret crush will stay secret…for now. Sooner or later, I’ll figure it out.

Castiel: [Growing a bit bolder] If it helps…one physical feature that I do find very attractive are green eyes.

Dean: …Someone you know with an attractive soul and green eyes. [Thinks hard for a few moments] Yeah, still no clue. But I’m telling ya, I’ll figure it out one of these days!

Castiel: [Simultaneously relieved and disappointed] Perhaps one day…

Dean: How about me? Think you can figure me out?

Castiel: You have already stated that you like dark hair best…long and wavy dark hair, that is…and although you have had many partners, your most long-term relationships are always with people who, to me at least, act level-headed. A level-headed person with dark hair…that is long and wavy.

Dean: …Yeah, you uh, pretty much hit the nail right on top of the head there. ‘Cept for one thing, and I’m not surprised you missed it: eye color.

Castiel: Eye color? [Unable to look right at Dean] Would you by any chance…like blue eyes?

Dean: [Slowly nods his head] Yeah, how’d you know? I mean, any eye color can be pretty, but blue’s the best.

Castiel: [Smiling hopefully to himself but still refusing to look at Dean] …Lucky guess.


	53. Question #52: What does your best friend talk about all the time?

Castiel: Dean regularly enthuses over his triumphant encounters with the supernatural.

Dean: Not all of ‘em are completely triumphant, so you’ve gotta enjoy the ones that are, you know?

Castiel: You also enjoy sharing stories of your various exploits in bars, whether you have earned money, alcohol, or a random woman’s affections.

Dean: I just enjoy sharing triumphs, like you said. Gotta take what you can get in the grisly hunting life. You, on the other hand, are usually all business, all the time. You oughta loosen up more, maybe revel in the exploits of a bar with me sometime!

Castiel: I am capable of “loosening up,” though I employ different methods than you.

Dean: Right, that’s the other thing you always talk about: every single time you see an animal, you text me about it. _Every. Single. Time._

Castiel: Animals put me at peace. They are not weighed down by the existentialism that comes with humanity, wrestling for meaning and purpose in a world that does not easily provide either. They simply live their lives with primal survival as their foremost goal, blissfully unaware of the ups and downs of complex consciousness and the recurring impending threats to existence as we know it.

Dean: …Right, you stick with bein’ philosophical about wild animals, I’ll stick with barhopping.


	54. Question #53: What would your friend do if they won the lottery?

Dean: Actually, I did win the lottery once! A few times in a row, actually…there was a cursed rabbit’s foot involved, long story.

Castiel: I’d like to think that you’d be responsible with your earnings and set aside some money, but seeing as you and Sam still must commit credit card fraud and scam people to get by, I’m assuming you already spent your prize.

Dean: Actually, I _was_ gonna set aside some. Problem is, I never got to claim my money.

Castiel: Why is that?

Dean: [Glares off into space] _Bela_.

Castiel: I’m not familiar with that name.

Dean: Be glad that you aren’t. She was a thorn in our side for quite a while.

Castiel: In all honesty, I’m not entirely sure what I would do if I won a large sum of money…

Dean: I bet you’d donate at least some of it. To…I dunno, the International Fund for the Protection of Bees? If that exists?

Castiel: I would take satisfaction in being charitable with my money, seeing as I wouldn’t particularly need it. I would happily let you and Sam have as much of it as you required, since you have to work so hard to get what you need to protect people.

Dean: …You are seriously an actual _angel_.

Castiel: Yes, Dean, I am…literally an angel.

Dean: No, I meant…never mind, you’re just a really good person, okay?

Castiel: [Blushing] I am not sure how to feel about being held in such high regard, but…thank you, Dean.


	55. Question #54: How many kids does your friend want and what will their names be?

Castiel: From my understanding, it is rather difficult to have children as a hunter.

Dean: Yeah, settling down is pretty much off the table for me at this point; unless by some miracle most of my circumstances do a 180.

Castiel: Still, I could truly picture you as a father. You briefly cared for Ben Braeden as a father would, did you not?

Dean: [Smiles forlornly] Yeah, yeah I did…

Castiel: And in many respects, you practically raised Sam. You would make an excellent father.

Dean: Too bad I can’t put any of that to good use…what about you? Kinda hard for angels to have kids too, huh?

Castiel: With the risk involved of producing unstable genetic hybrids such as nephilim, it is rather difficult. But if I were truly in a position to care for children of my own…I could adjust to the idea.

Dean: You could totally be a dad!

Castiel: Perhaps…all the same, I think I would only want one child. Anything more than that would be too overwhelming judging by my encounter with a baby when I was human…

Dean: I’m gonna have to agree with that. One kid’s enough to start with.

Castiel: If you did have a child, would you name them after your family? Perhaps your mother or father?

Dean: …That’s what I always thought I’d do. Yeah, a little Mary or John, or hell, even a tiny Bobby… [Cracks a little smile]

Castiel: I believe this is what you would refer to as “a chick-flick moment.”

Dean: [Still smiling] Shut up.


	56. Question: #55: If your friend could have one superpower, which one would it be and why?

Dean: Cas is already basically a superhero with all the powers he’s got.

Castiel: I have been missing one of great importance since Metatron’s interference, though.

Dean: What? [As it dawns on him, he becomes more subdued] Oh, your…your wings, right?

Castiel: [Solemnly] Yes, my wings. I have not been able to engage in flight or teleportation the way that I am used to because of the damage inflicted to them. They will heal, but I have no idea how long that will take…

Dean: Jeez, that sucks…so even though you’ve still got all your other awesome powers, the one you’d want back is flight, right? ‘Cause you miss it?

Castiel: I miss it dearly. One day it will return to me, but until then, I will wish for it back.

Dean: You’ve got a lot more to pick from for me. What do you think I’d want, huh?

Castiel: Hmm…I believe an abnormal degree of speed and agility would suit you best. It would prove useful to your hunting and your attempts at multitasking.

Dean: …I was gonna say I’d want Batman’s power of being super rich, but that actually sounds better.


	57. Question #56: If your friend could choose to master one skill, which one would it be?

Dean: In my opinion, mastering socializing would probably suit you best.

Castiel: That would make many aspects of my life much easier, so yes, I would have to agree with you.

Dean: I’m pretty good at most of what I need to do…talking with people, hunting, driving-

Castiel: Driving? I understand that you are a capable driver, but you regularly disobey road signs and speed limits.

Dean: …Y-yeah, well, maybe I’m so good that I don’t _need_ road signs to tell me what to do. There are hardly ever any other cars on the backroads I take anyways.

Castiel: I would still prefer that you heeded the rules of the roads you drive, if only for my own comfort. I worry about your well-being.

Dean: It’s nice of you to worry about me, Cas, but really, I’m-

Castiel: _That_ is what skill you should master: safety. Although your risk-taking occasionally pays off, it is the instances where it backfires that lead to the worst of consequences for you.

Dean: …All things considered, that would actually be useful. Maybe that’d make some hunts turn out better.


	58. Question #57: What was your friend’s first job?

Castiel: I don’t recall you ever mentioning having a job, at least outside of the ruses you pull on cases.

Dean: Never really had time…keeping a job is next to impossible when you’re constantly moving across the country. [Snaps fingers] One time, Sam and I worked as carnies for a while to stop a killer clown! Oh yeah, and I could never forget my stint as a substitute gym teacher.

Castiel: But you do not recall your first “job?”

Dean: [Shrugs] Technically, bein’ a hunter was my first job. And what about you? I guess you were always just a soldier in the garrison, huh?

Castiel: …Actually…before I was officially trained for the garrison, I was an assistant sentry. I kept watch of developments on earth for a while. Even after I rose to become a soldier, I still kept an eye on the planet’s growth in what little free time I was afforded.

Dean: Huh…did it pay well?

Castiel [Stares at Dean briefly] Angels do not get paid, Dean.


	59. Question #58: What was the shittiest job your friend ever had?

Dean: Sounds like heaven gave you a pretty good deal with your duties. Which one was shittier, bein’ a soldier or sentry?

Castiel: Looking back, I would have preferred to remain a sentry, so in that way I suppose my post in the garrison was inferior. But then again…if I had never been a soldier, I never would have met you and altered the course of my existence.

Dean: So it all evens out…man, you’re lucky you never had to deal with a shitty job. Because here on earth, there are plenty of them.

Castiel: Such as…?

Dean: Probably one of the worst ones I’ve had to deal with is being a coroner. Technically I was never actually a coroner, it’s just another ruse I pull out for cases sometimes, but some of the dead bodies I’ve seen… [Cringes] Just when you think you’ve seen it all, some poor schmuck dies in a whole new horrific, gruesome way. Sam and I have to be the ones who drop in to examine them, and…it’s just _gross_ , alright?

Castiel: I recall a couple of occasions when I accompanied you and Sam to examine bodies for your cases. I wasn’t affected by the sight, but I can understand how humans would find it revolting.

Dean: …Maybe we ought to bring you along on more body examinations in the future. One less thing I’d have to gag at.


	60. Question #59: Who is your friend’s favorite YouTuber?

Castiel: …What’s…a…?

Dean: I think it’s an internet thing. Like, someone who makes videos on YouTube.

Castiel: Oh, I see…I’m not particularly familiar with that platform or many of the people who use it. I have briefly encountered some videos of a man documenting his efforts to care for various colonies of ants…I believe he went by the name “Ants Canada.”

Dean: You watch videos of ant farms?

Castiel: Ant society and behavior are fascinating to observe.

Dean: …You friggin’ _dork_.

Castiel: There have been a few instances of me finding you watching videos on the YouTube. Usually they contain compilations of humans or animals making mistakes and in many cases suffering mild bodily harm as a result.

Dean: Oh, you mean the Fail Army videos? Yeah, those are hilarious!

Castiel: I fail to see what is so amusing about these compilations of failure.

Dean: They can be good for a pick-me-up! Someday I am sitting you down and we are watching a Fail Army playlist until you can laugh at them along with me.

**Notes for the Chapter:**

> Ants Canada is actually a really cool YouTube channel that I would recommend checking out. I enjoy his videos.
> 
> ...Or maybe I'm just a dork like Cas. ;w;


	61. Question #60: What was a weird dream your best friend had?

Dean: You don’t even dream, do you? Since you don’t sleep?

Castiel: That is correct. Even when I was without my grace, I couldn’t recall dreaming, or at least I had no dreams that were significant enough to remember.

Dean: That’s lame. Dreams can be fun! Not so much with nightmares, but hey, you get a taste of the good and the bad.

Castiel: I have visited your dreams in the past.

Dean: Woah woah woah, dreams as in _plural_? I only remember you showing up in my fishing dream that one time.

Castiel: …I…may have observed a few others in the interest of maintaining contact with you.

Dean: [Getting a little angry] So you’ve been poking around in my head, is that it?

Castiel: Not in a long time! I promise, Dean, I only intended it to check on you when I was otherwise physically occupied elsewhere. I have seen nothing incriminating, if that’s what you’re concerned about.

Dean: I still dunno how I feel about that…but I guess better you than some other stalker angel. Do I _wanna_ know what the weirdest thing you saw in my dreams was?

Castiel: The oddest dream I encountered involved two…rather scantily-clad women dressed as human interpretations of an angel and demon. I left that one rather quickly.

Dean: Great, first Anna popped in on that one and now you have, too. Of all the recurring dreams… [Shakes his head to collect himself] Whatever. I don’t have that one anymore. Sure you didn’t see anything else?

Castiel: No, I…I have seen nothing else. There was one dream involving you and a dreamt version of me, but…

Dean: [Eyes nervously snap up] B-but?

Castiel: …It was merely a memory of you and I watching television together. Seeing as you already had a version of me there, I left shortly afterwards.

Dean: [Extremely relieved] Oh, okay, good. I-I mean, good that you saw nothing going on. Just…us watching TV. That was it. Just like in real life. Ha.


	62. Question #61: If you grew up together, what’s a funny story from your childhood?

Dean: Well, we definitely didn’t grow up together. We could just share funny stories from our own childhoods instead.

Castiel: Very little in the way of humorous things occurred in my “childhood,” if it could even be called that. I suppose Gabriel teaching me to fly as a fledgling is somewhat noteworthy-

Dean: Back up. _Gabriel_ taught you how to fly?

Castiel: He kept a close eye on me for my first few hundred years or so…his preferred method of teaching fledglings to fly was throwing them off places of great height and swooping in to catch them at the last moment. He would repeat this until they figured out how to use their wings.

Dean: …Why can I picture that so clearly?

Castiel: My brother was always a trickster, even before taking that guise here on earth.

Dean: Tell me this: on a scale of one to ten, how cute of a baby were you?

Castiel: I wasn’t really a “baby”, rather a small celestial wavelength, so I’m not sure how one would gauge that based on the human attribute of cuteness.

Dean: …Right, never mind then. Let’s see, funny story from my childhood… [Chuckles under his breath] First one that always comes to mind is when Sammy dressed up like Batman and jumped off the shed…he was only five, ended up breaking his arm. But to be fair, I’d been dressed like Superman and jumped off the shed before him.

Castiel: So in short, we’ve both had experiences in which an older sibling led a younger sibling off of a high surface.

Dean: …Maybe our childhoods have more in common than I thought.


	63. Question #62: Does your friend focus on the future or the past?

Dean: For a being that’s been around as long as you have, you seem more focused on the future.

Castiel: Although I have a long past, the new path I have set out on since rebelling against heaven has completely changed the course of my fate. I have little choice but to look to the future.

Dean: Makes sense…

Castiel: You are more oriented towards the past, it would seem. You enjoy reminiscing, but you are also frequently troubled by certain aspects of your past.

Dean: Guess I’ve got rearview vision. Which…isn’t a bad thing, right?

Castiel: Not necessarily. It may be useful, but it also lends itself to holding grudges… [Looks pointedly at Dean]

Dean: What, I can forgive and forget! It just…takes a while.

Castiel: [Nods dismissively and turns back to the list] Mmm-hmm.


	64. Question #63: You want to make a sandwich for your friend. What do you put on it?

Dean: Honey. Definitely honey, and peanut butter and jelly. Dunno if all those would go well together, but since you’re apparently a fan of PB&Js, it’d work for you.

Castiel: I did develop a taste for peanut butter and jelly sandwiches during my time as a human. I have missed their taste an awful lot…I don’t recall ever informing you of that, though.

Dean: A little- er, big moose told me.

Castiel: I would enjoy trying that sometime…

Dean: Next time you feel up to a sandwich, we’ll getcha a Honey PB&J. We can call it the Castiel Special!

Castiel: I once constructed a sandwich for you during the rise of the Leviathans. Uncontaminated ingredients were hard to come by, so I had to be especially careful…

Dean: [Snaps to awareness at the memory] Oh, yeah! I dunno if I ever told you this, but that sandwich was awesome! Maybe Sammy really is on to something about using organic ingredients…or maybe you’re secretly just really good at making food.

Castiel: [Shyly] I…wouldn’t say that. The one time I tried to make a pie for you, I-

Dean: Nearly burned down the oven, yeah, I remember. Just stick to making stuff that doesn’t involve fire and you should be fine.

Castiel: So if I were to make a sandwich for your consumption, I would attempt to replicate what I did before using fresh wheat, lettuce, tomato, and humanely-slaughtered ham.

Dean: Sounds like a lot of hard work to me. You could always just find one at a deli somewhere.

Castiel: [Resolutely] It wouldn’t be the same. Sam is correct in saying that organic ingredients make all the difference.

Dean: …Jeez, he _is_ brainwashing you with his health-freak propaganda, isn’t he?


	65. Question #64: What’s your friend’s favorite drink?

Castiel: Based on my observations, Dean enjoys most any drink that contains alcohol.

Dean: [Defensive] That’s not all! I drink coffee, too!

Castiel: Most often he can be found consuming beer at inopportune times.

Dean: [Mumbling under his breath] Says Mr. “I Found a Liquor Store and I Drank It.”

Castiel: Although I will admit that since coming to inhabit the bunker, Dean has begun to consume a higher ratio of coffee. I can understand the need for coffee. I’d never thought that bitter bean water could be such a lifesaver, but when I was human…I’m not sure I would have survived my mornings without it.

Dean: Don’t see you drinking much coffee anymore. Now you’re all about fancy herbal teas and whatnot…

Castiel: Tea is a relaxing, warm beverage that I find I am able to enjoy even as an angel.

Dean: _And_ you can pour unholy amounts of honey into it.

Castiel: …And I can add a large portion of honey to it, yes.


	66. Question #65: Who’s the better dancer?

[They both look at each other momentarily.]

Dean: I…don’t…think I’ve ever seen you dance before.

Castiel: …It isn’t something that comes naturally to me.

Dean: Have you ever even tried?

Castiel: No, I have never attempted-

Dean: [Claps hands together] You. Me. Dance off. _Now._

Castiel: [Nervous] Right this very second? I-I’m not sure that’s…what about the dessert vouchers that await us at the end of this assignment? A “dance off” would delay you getting to receive your pie.

Dean: [Considers this and slumps back into his chair] Fine, you’re right. But next chance we get, you are showing off your moves. Until then, I will retain my title as “best damn dancer in this bunker.”

Castiel: I was under the impression that Charlie was a skilled and enthusiastic dancer when left to her music.

Dean: …Okay, I’ll retain my title as “best damn dancer in this bunker except for when Charlie’s here.”


	67. Question #66: Who’s a better singer?

[Again, they both look at each other.]

Castiel: I can be reasonably convinced to compare our dancing abilities, but I-I am not certain about singing.

Dean: Listen, buddy, don’t even worry about that. I, uh…I’ll be the first to admit that I’m not exactly the best singer around. [Cringes] God, if I have to remember the karaoke incident from when I was a demon one more time…

Castiel: I can’t recall ever personally hearing you sing, but surely you’re not _that_ bad-

Sam: [Chiming in from another room] No, he really is! You try sitting shotgun and having to listen to him belting off-key Metallica for years on end.

Dean: [Shouting to the side of the screen] Shut up, I’m a joy to drive with!

Castiel: …All the same, I should doubt that your voice would be any worse than mine. I am hardly tuned for singing.

Dean: You told me that you sang a lullaby to that baby that one time, right? C’mon, if you could lull a baby to sleep, your singing can’t be half-bad. You oughta let me hear it sometime!

Castiel: Perhaps…I will consider it for the future.


	68. Question #67: Who’s better at math?

Dean: Seeing as I never excelled in school, I’m gonna give the point to Cas here.

Castiel: But neither of us has demonstrated our mathematical capabilities.

Dean: Just trust me on this. Whenever I ended up in a math class, I shook it off. Numbers weren’t really my strong suit. And you’re really smart, so…

Castiel: While my angelic nature allows for a range of swift numerical calculations and probabilities, intelligence should not be measured by math alone. You’re extremely smart too, Dean; just in other areas. You possess great knowledge of mechanics, social skills, and pop culture to name a few. Don’t judge your own intelligence by your math skills or lack thereof.

Dean: …Okay, for once I wasn’t actually trying to beat myself down, but thanks for the reassurance, Cas.

Castiel: It sounded like self-doubt to me. I wanted to ensure that you were not unnecessarily feeling badly about yourself. I will take any chance I can to combat your self-loathing.

Dean: Man, it would have been nice to have you around back in school…

Castiel: To help boost your self-esteem?

Dean: [Grins] No, to help me ace my math tests.


	69. Question #68: Who’s better at talking to people?

[Castiel just looks towards Dean and stares.]

Dean: Yeah, uh, gonna have to say that’d be me.

Castiel: I find your social skills greatly admirable. My efforts to imitate them have…not always been so successful.

Dean: You’re just an awkward, dorky guy. You can’t help it!

Castiel: Is lacking social skills a feature of being a “dork?”

Dean: In your case, definitely. But you know what, I think it’s kinda charming in its own way. Some people really dig the whole socially awkward shtick. It’s cute!

[Castiel tilts his head as Dean’s words settle in. Dean goes a near unprecedented shade of red and fumbles as he rushes to amend his statement.]

Dean: I-I mean, a lot of people find it cute! I wouldn’t know, really- I mean, it _is_ but I- what I’m _trying_ to say is-

Castiel: [Clearly pleased] I’ll take that as a compliment.

Dean: [Sinks down into his chair and tries to discreetly hide his face] Yeah, don’t mention it…


	70. Question #69: Who’s the better cook?

Dean: For all his organic sandwich-making skills, Cas isn’t much of a kitchen connoisseur.

Castiel: I believe the incident in which I attempted to bake a pie speaks for itself.

Dean: It was a nice thought, Cas, but just stick to picking one up from the store next time.

Castiel: Dean’s cooking is, in my exposure to it, rather tasty. I do wish you would make food more often when I am around; I would enjoy sampling more of your cooking.

Dean: Really? [Holds himself with pride] Well then, whenever you’re up to it, just lemme know and I’ll spread out a full-course meal for ya.

Castiel: [Smiles] If it’s no trouble, that would be lovely.

Dean: [Points a finger at Castiel] Just don’t defile any of it with your honey unless you have to, alright?

Castiel: …Understood.


	71. Question #70: Who handles their money better?

Dean: Dude, do you even need money?

Castiel: If I intend to go out and purchase resources or commodities, yes; although I do require significantly fewer than a human would, so I spend very little.

Dean: Alright, I guess that makes sense…but are you a smart spender?

Castiel: I keep some money set aside as savings, and seeing as I rarely have to spend my funds, I’d say that I have reasonably stable finances.

Dean: Where are you keepin’ all this money? I can’t exactly see you opening up a bank account.

[Castiel nonchalantly reaches into one of the inner pockets of his trench coat. He produces several wads of crumpled bills on the table. Dean stares.]

Dean: You just…carry all your cash. On you. At all times.

Castiel: I keep another portion of my savings in my vehicle.

Dean: [Sighs] The sad thing is, that still beats me. Wish I could say that I have savings stored up somewhere, but uh, ammunition ain’t exactly cheap. And I’ll admit, I have been known to blow cash on impulse purchases in the past. Sammy and I have still gotta get by on credit card scams whenever we can.

Castiel: If you ever need financial support, I can certainly contribute some of my own money and help you to better balance your own.

Dean: …You really are embracing the “holy tax accountant” persona, aren’t you?


	72. Question #71: Who’s more reliable?

[An awkward silence settles.]

Dean: [Laughs nervously] We’ve both kinda screwed each other over in the past, but…

Castiel: Considering my past wrongdoings, I would daresay that you are the more reliable of the two of us. You have a certain degree of consistency that I can rely upon no matter the circumstance, always staying true to the core of your soul as I know it.

Dean: Dude, c’mon! I’ve had my fair share of wrongdoings too! I can be unfair sometimes, I’ll admit it, but you always stick with me no matter how unfair I get. I said it before, you’re a steadfast friend. I can always rely on you to do what you think is right.

Castiel: But just because I think that something is right does not mean that it _is_ right, Dean. Taking the souls of purgatory into my vessel allowed the Leviathans to escape into our world, no matter my good intentions, and that is only one of numerous examples. I am more of a liability than anyone to be relied upon.

Dean: Like I’m much better! Hell, I took the Mark of Cain ‘cause I thought it was the only thing that’d stop Abaddon, and you and Sam nearly had to die because of that hasty decision! It even turned me into a demon; how can you possibly rely on someone who’s been a demon?

Castiel: That is hardly a fair example. You were not yourself when you were a demon, and you took the Mark for a heroic purpose. It is your stark heroism that makes you so reliable; I can always count on you to rise to the challenges we face to the best of your ability.

Dean: Well _you_ have shown loyalty that reeks of reliability at almost every turn. Even when we’re about to run headfirst into a suicide mission, I can always count on you to be right there by my side, no matter the odds.

Castiel: But if you take into account-

Sam: [Shouting from another room again] Oh my god, you guys, you’re _both_ reliable. Let up on the cycle of aggressive praise and self-pity and just accept it as a tie, alright? I can’t stand to listen to more of this.

[Dean and Castiel stay silent, glancing off-camera towards Sam’s voice. Slowly, they turn back to each other and reluctantly nod.]

**Notes for the Chapter:**

> Gosh diggity dang it guys why can't you just love yourselves like you love each other ;w;


	73. Question #72: Who’s more annoying?

Dean: Depends. Are we talking annoying like poking fun and harmless teasing, or _sending strings of texts at three A.M. in the freakin’ morning?_

Castiel: That was one time, Dean. It had slipped my mind that humans were normally asleep by that hour.

Dean: Precious four hours, man. Can’t function without them.

Castiel: I’ll admit that I send you many texts, but you are the person I speak with the most. I enjoy conversing with you, even over a digital format. [Turns resigned] But, if you would prefer that I lessen the number of texts I send you, I can limit how often I contact you-

Dean: [Getting a little frantic] Uh, wait! I didn’t mean- don’t stop texting me, please. I like texting with you too. Just…not at three A.M.

Castiel: I will take precautions to make sure that does not happen again.

Dean: [Still feeling bad about putting Castiel down] Your texts aren’t annoying, really. I just act dumb about ‘em ‘cause I feel like that’s what I’m supposed to do. Every time I see that I have a text from you, it makes me smile.

[Castiel brightens considerably. Dean shifts uncomfortably but still forces himself to keep his focus on Castiel.]

Dean: Honestly, I’m the more annoying one. The jokes I crack…I kinda mean for some of ‘em to be annoying. Blame it on years spent being Sam’s big brother.

Castiel: Even if much of your humor escapes my understanding, I find it to be endearing rather than annoying.

Dean: [Flushing slightly] N-not everyone else does, though. Just let me be the annoying one, alright? You’re not annoying, you’re just…

Castiel: A dork?

Dean: Yeah, exactly. [Smiles] A dork.


	74. Question #73: Who always gets their way?

Castiel: Considering our circumstances, neither of us usually get precisely what we want.

Dean: Yeah, but between the two of us, whose will would win out?

Castiel: We can both be rather stubborn…

Dean: That’s true.

Castiel: And we have butt heads over the proper course of action on more than one occasion…

Dean: Also true.

Castiel: But seeing as you unofficially act as the “leader” of our group, I would say that you get your way most often.

Dean: [Falters] You lost me. “Leader?”

Castiel: Although our team does not technically have an appointed leader, you naturally fill that role when it is needed. All of us contribute to making decisions and planning, but in many cases you take charge. It may simply be an effect of you being used to the role of “big brother.”

Dean: …I’m not, like, a dictator all the time, right? I mean, I know that for a while I was, ‘cause I literally said that, but-

Castiel: You are far from a dictator despite your stubbornness. You have an excellent sense of focus and perseverance. I find that inspiring.

Dean: …But that’s still not gonna stop us from butting heads over stuff, is it?

Castiel: More than likely it won’t. That’s just part of our relationship I suppose. We are both stubborn individuals in our own ways; someone has to keep each of us in line.


	75. Question #74: Who is more extroverted/introverted?

Dean: You’re basically a classic example of a socially awkward introvert. Not that social awkwardness and introversion are exclusive or anything, but…

Castiel: No, you’re right, I am most definitely what you would call an introvert. And you are a classic example of a brash, outgoing extrovert.

Dean: Cool, so we’re like opposites!

Castiel: And as they say, “opposites attract.”

Dean: …I…don’t think that means what you think it means.


	76. Question #75: Who is more optimistic/pessimistic?

Dean: Kinda hard to be an optimist when you’re livin’ our lives. And even though you keep on fightin’, no matter what, life tends to kick you to the curb when you’re a hunter.

Castiel: That may be true, but there is always at least a small glimmer of hope to lead us towards success. There is always some form of triumph to be attained.

Dean: …I think we just answered the question.

**Notes for the Chapter:**

> This one's really short sorry ;w;


	77. Question #76: Why is your friend a great friend?

Dean: Okay, where do I begin.

Castiel: I’d assume with whatever first comes to your mind that makes me, in your eyes, a “great friend.”

Dean: …You say that like you doubt that you are.

Castiel: Considering our history and some of my actions-

Dean: No, no no no, shut up. You are _not_ going on a self-bashing spree while I’m trying to sing your praises. For once, you’re just gonna sit there and try to feel good about yourself, capiche?

Castiel: [Grumbling] …Yeah, I capiche.

Dean: …Okay, good. Now, I know I said it before, but you are steadfast, and loyal, and reliable. Even if you’re a little starry-eyed sometimes, you always use that to do what you think is right. And…jeez, I’m just repeating myself! I need some new material here.

Castiel: You needn’t stress, Dean, that’s plenty.

Dean: Nope, I’m not done yet. Let’s see…you’ve got smarts, you’ve got resolve, you’re some kinda gentle bee-communing-nature-guru, _and_ you’re a total badass at the same time. One second you could be kneeling in some garden, talking to flowers or something, and the next you’ll be out smiting an army of demons with your bare hands. You always look out for me and let me feel like I’m actually safe, you make me laugh without even havin’ to try, and always just when I need it... oh, and did I mention that you’re a huge freakin’ _dork_ and just how adorable that is?

Castiel: [Looks at Dean with wide, surprised eyes] You…think I’m “adorable?”

Dean: [Blushes, but determined to make Castiel feel good about himself, maintains his resolve] Y-yeah, in your own dorky way, yeah, you are…

Castiel: [Not sure what to do with this treasured new information] …Th…thank you, Dean.

Dean: Yeah, no…no problem… [Shakes himself a little] But seriously, you’re just awesome, okay? You know that, right?

Castiel: Oddly enough, hearing it so sincerely from you…some part of me believes it.

Dean: [Cracks a smile] …Good.

Castiel: I will do all in my power to return the favor to you. You deserve to feel just how “awesome” you are as well.

Dean: C’mon man, you don’t have to do that, not like I did-

Castiel: Yes, I do. I would like to. And since I complied with your wish to sit quietly and let you shower me with praise, it is only fair that you do the same.

Dean: …Alright, fair enough. Have at me.

Castiel: As I have stated multiple times since beginning this list, you are heroic, brave, and selfless to a fault. You put others’ lives before your own safety, and though that worries me, that doesn’t make it any less admirable. Since the first time I fell, you have been there to show me the ways of humanity, to welcome me into your small family, and you’ve given me a home to come back to. You have helped me more than I deserve; I don’t believe I’ve ever expressed just how grateful I am for that. So…thank you, Dean, truly.

Dean: [Still uncomfortable with so much praise] It’s no problem, really. It’s what anyone else would have done.

Castiel: Not just anyone else, Dean. You’re different. Your soul is…unique. It’s unlike any other I’ve ever seen. That’s how I know your heroism is deep and true. Besides that there is, of course, your charisma. As I am not very socially skilled myself, I look up to that trait. Instead of leaving me to flounder in social encounters, you attempt to help guide and teach me, and you’re willing to listen to me even when I struggle to articulate. And in all honesty…I find you quite charming.

Dean: Ch-charming, huh? [Manages a smirk] Well, what can I say? I have that effect on people.

Castiel: [Flushes a little] Yes, you do…


	78. Question #77: What’s a moment in your friendship that touched you?

Castiel: I find that we touch each other’s shoulders often, if that’s what this question means.

Dean: No, Cas, it means like something that hit you emotionally. [Sighs] Which means more chick-flick moments.

Castiel: I don’t understand your aversion to “chick-flick moments.” In my experience, they’re endearing and positive experiences.

Dean: …Right. Anyways, the question. [Quietly whistles] There’s, uh, there’s a lotta stuff that’s happened with us…

Castiel: There have been many emotionally touching moments between us.

Dean: [Hums with laughter] You know, I always find myself thinking back to when you were waitin’ for me to get my four hours that one time. Then that dick Zachariah- sorry, I know he was your brother, but he _was_ a dick-

Castiel: [Nods his head] No argument here.

Dean: But yeah, he sent me into the future, and… [His face darkens] God, some of the stuff I saw there, I just…I was…and you were… [He trails off and shakes his head] Next time I saw you was when you swooped in to save my ass from Zach, and it just kinda hit me while we were standing on that roadside afterwards how lucky I was to have you as you were. Made me realize that I… [Realizes how deep he’s gotten and backtracks, coughing into his fist] That I r-really value you as a friend. I knew then that we’d stick together…pretty much forever.

Castiel: [Breaks out into a soft smile] I still remember that…I have done my best to follow your advice to "never change." I’m…not sure that I have succeeded, but-

Dean: Nah, you’ve done good. You’re still a dork after all this time.

Castiel: Now then…as I said, there are many of our shared moments that have “touched” me as it were, even spanning back to when we first met, but one of the most significant was during Dick Roman’s attempted takeover. When you took me along to retrieve your car, you talked me into joining you on your mission to kill him. And you said to me…

Dean: That whole “cursed or not” speech?

Castiel: Yes, that was the one. I was surprised enough by the effort you put into trying to convince me; I was being unreasonably difficult at the time and looking back, I understand much of your frustration towards me. Yet when you said that…even in my mentally-altered state, it emotionally “hit me” as you put it, enough so that I agreed. I couldn’t fathom what would make you say that to me with how I’d been acting, and at the time I…I thought I’d figured it out, but I haven’t been so sure since, I may have jumped to wishful conclusions and I-

Dean: Don’t hurt yourself, buddy. Slow down a little.

Castiel: Right…regardless of what may or may not have spurred you to say it, it touched me. It’s a memory that I hold dear, and in my opinion, it exemplifies the value of our bond- er, friendship, if you would prefer to call it that.

Dean: You know what, call it a friendship or partnership or “profound bond” or whatever you want. Maybe you’ve just got me in a sappy mood with all this chick-flick crap, but I really don’t care right now.

Castiel: [Genuinely surprised] Oh…well, in that case, I think it exemplifies our profound bond. That would be a lovely note to end this list on, would it not?

Dean: Gonna have to say yeah. I, uh, had no idea that moment meant so much to you, but…I’m glad it does, I really am. Kinda meant a lot to me, too…

[The two smile and stare at each other for uncomfortably long. Dean abruptly pulls his gaze away and shoves his chair back.]

Dean: [Looking towards the side of the room] Right, okay, we’re done. How about those dessert vouchers?

Charlie: [From just off-camera on the sidelines] Alright, a deal’s a deal. Here you go: two free dessert vouchers.

[Charlie’s hand comes into frame, slamming two coupons down on the table in front of Castiel and Dean. Dean breaks into a huge grin and swipes them up, jumping to his feet.]

Dean: Alright, now this is what I’m talkin’ about! Free pie, here I come!

[Castiel calmly pushes back his chair and rises to his feet. Dean slings an arm around his shoulder and begins guiding him out of the frame. His voice can be heard slowly getting farther away as they leave.]

Dean: C’mon, I promised you ice cream. You gotta try at least a few flavors to make sure you know which is your favorite, but I still think you’re a vanilla man…

[Charlie laughs to herself from off-camera. She steps partway into the frame and shakes her head after them.]

Charlie: [Turning to the camera] Well, it didn’t get them to outright admit their huge crushes on each other…but it got them a hell of a lot closer.

[She reaches for the camera. A click is heard and the screen cuts to black as the video ends.]

**Notes for the Chapter:**

> Ahhh I really didn't want this story to end. ;w; I've had too much fun writing it, jeebus. It's been great practice for writing Dean and Cas, and I still feel like there's a lot to explore here.
> 
> Sooooo instead of letting this go, I'm working on doing another story wherein SPN characters respond to a tag, and I have some more tags in mind after that. I think this will be a great chance to experiment with writing for more characters and having more fun along the way. In short, I'm turning this into a series because I have absolutely no self-control. Look forward to seeing the next in this series posted sometime in the future!! And thank you all for reading! :D


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